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Syntehsis method plant sterol or/and plant steroid alkanol-beta-D-glucoside compound

A technology of phytostanols and phytosterols, which is applied in the field of synthesis of phytosterols or/and phytostanol-β-D-glucoside compounds, and achieves the effects of simple operation, mild reaction conditions and easy availability of raw materials

Inactive Publication Date: 2003-09-24
上海药谷药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, there is no bibliographical report on synthetic preparation, so a method for industrialized production of phytosterols or / and phytostanols-β-D-glucosides is sought

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Recrystallization Purification of Crude Phytosterols

[0031] The crude phytosterol (20 grams, purchased from Jiangsu Spring Valley Biological Products Co., Ltd.) was dissolved in acetone (200 ml), and after it was fully dissolved in a water bath at 50° C., it was placed at room temperature for 4 hours, and filtered by suction to obtain 19 grams of white needle-shaped crystals. , after GC-MS analysis and test, its composition is consistent with the standard phytosterol, the content of each component is brassicasterol-3.52%; campesterol-26.52%; stigmasterol-24.11%; β-sitosterol-45.85%; The rate is 95%.

Embodiment 2

[0032] Example 2 Synthesis of five-O-benzoyl-D-glucopyranose (II)

[0033] Take D-glucose (30 g, 167 mmol) and add it to pyridine (330 ml), add benzoyl chloride (107 ml, 915 mmol) dropwise under ice-water cooling, stir and react overnight at room temperature, then add methanol (13.5 milliliter, 334 mmol) to quench the reaction, the solid-liquid mixture is poured into hot water, a large amount of solids are precipitated, filtered, washed with water, and the solid is dried to obtain 112 grams of crude product, which is five-O-benzoyl-D- Glucopyranose (II), the HPLC test result shows that the purity is 97.21%, and the yield is 99%.

Embodiment 3

[0034] Example 3 Synthesis of 2,3,4,6-tetra-O-benzoyl-D-glucopyranose (III)

[0035] Penta-O-benzoyl-D-glucopyranose (II) (617.3 g, 0.857 mol) was dissolved in N,N-dimethylformamide (3000 ml), and glacial acetic acid (103 ml, 1.8 mol), ice-water bath, dropwise added hydrazine hydrate (100.8 g, 1.8 mol). After reacting for 1.5 hours, it was diluted with 6000 ml of ethyl acetate, washed twice with saturated saline, 4% hydrochloric acid solution, saturated aqueous sodium bicarbonate solution, and saturated saline, and dried over anhydrous sodium sulfate. Filtration, concentration, column chromatography (wet column, eluting with 4:1 petroleum ether and ethyl acetate, developing solvent PE:EtOAc=3:1), gave 393 g of solids, which were 2, 3, 4 , 6-tetra-O-benzoyl-D-glucopyranose (III), the purity of HPLC test result is 95.89%, the yield: 74%.

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Abstract

The present invention relates to a method for synthesizing polytosterol or / and phytosteroalkanol-beta-D-heteroside compound. Said method includes the following steps: recrystallizing and purifying the phytosterol or / and phytosteroalkanol crude product to obtain crystal, then making said crystal and polysubstituted-D-glucose trichloroethylene imine ester produce glucosidation reaction in the presence of Lewis acid catalyst, and then removing protecting group so as to obtain the invented phytosterol or / and phytosteroalkanol-beta-D-heteroside compound.

Description

technical field [0001] The present invention relates to a kind of synthetic method of phytosterol or / and phytostanol derivative with physiological activity, specifically a kind of synthetic method of phytosterol or / and phytostanol-β-D-glucoside compound method. Background technique [0002] Phytosterol or / and phytostanol-β-D-glucoside (phytosteryl-β-D-glucoside) is a derivative of phytosterol or / and phytostanol, usually with phytosterol or / and The coexistence of phytostanols is a kind of vegetable fat widely present in many plants (including vegetables and fruits). In recent years, some studies have shown that phytosterols and their glucosides have many important physiological activities for the human body, thus triggering the People's great interest. [0003] What is more noteworthy is that phytosterols or / and phytostanols-β-D-glucoside also exist in many traditional Chinese medicinal materials, such as ginseng, eleuthero, carrot seeds, sheath nuts, etc.; among them, the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
CPCY02P20/55
Inventor 惠永正刘俊耀何亚楠
Owner 上海药谷药业有限公司
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